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Dear Guy,
I know we’ve had our fair share of ups and downs since we’ve known each other.
I know neither of us is quick to trust or communicate our feelings.
But I also know that if I could do anything (and I mean anything) all I wanna do is fix you.
You’re not broken, per se, but life hasn’t always been kind to you.
You’re not great with trust because no one has given you a reason to trust.
I’d like to be that reason.
I know these are just words so it might not count for much, but it’s pretty much all I’ve got.
I love you.
Sincerely,
Calhoun

Dear Drunk Guy on the Corner,
I don’t know if anybody’s told you this, but you- you’ve clearly soiled yourself.
I mean- I don’t even know how to describe it. It’s just so right fucking there.
Yeah, like, see how your blue jeans are one shade?
Then, there’s that one area on your crotch and down your leg that’s slightly darker?
That’s- that’s clearly urine, dude.
I just thought you should know.
Sincerely,
Calhoun

Dear Layla,
I’d like to take the opportunity to apologize for your human.
We aren’t all like that.
See, if there’s one thing that I cannot stand, it is irresponsible pet ownership
Naturally, you’re a puppy so it’s understandable that you’ll have an accident here and there.
I’m not thrilled with it, but I understand it.
Plus, given that your human only takes you out, roughly twice a day?
Yeah, bladder control could be an issue.
You deserve better than that.
Hell, any canine does.
So please, don’t hate us all cuz you got stuck with one of the bad ones.
Sincerely,
Calhoun

Dear Bar Patron,
There’s an art to complimenting someone.
How do I know that? I mean, you do raise a good point, I have not been known to compliment many folks.
In fact, you raise another good point, I’m not great at receiving compliments either.
They usually just make me feel wildly uncomfortable, while I quickly try to come up with a counter-compliment.
Before long, we’re in a compliment competition and I end up winning with the stellar, “That’s a sweet Mr. Roger’s sweater you’ve got…” (Don’t mock, it actually happened)
Still, the other night, that wasn’t just me. That was a weird compliment.
While “You’re hot, I wanna take you home in my trunk” was undoubtedly well-intended, it came off as more or less… well, date rape-y?
Yeah, that was the term I was looking for. Date rape-y. Seriously, dude, not your A game. Not even B or C game. Doesn’t even register in the English alphabet, that’s how bad it was.
But, um… thanks? It’s the thought that counts?
I dunno, I just thought somebody should tell you how awful that line is, in case you ever try it on somebody else and they wind up calling the cops on you.
Sincerely,
Calhoun

Dear Random Girl,
I’m doing my best not to make this sound like a Craigslist Missed Connection, but so far, I’m comin’ up empty.
See, I was just finishing up my run this morning, when I saw you getting out of the passenger side of a car.
As you walked up the steps of the building we both live in (See? Totally not creepy or stalkerish) I was struck by the little bow you had in your hair.
In an attempt to not be awkward, I waited a few moments before saying, ‘I know this is really random to hear from a sweaty shirtless stranger… but I really like the bow in your hair.”
Yeah, that “not awkward” thing? Nailed it!
Luckily, she smiled and politely said thank you before continuing up the stairs when I arrived at my front door.
In a last-ditch effort, I turned around and said, “Sorry, I hope that didn’t seem totally creepy. I just realized how weird I sounded.”
She laughed again and said, “No, it’s totally one of those random things that makes my day.”
See that, people? I made someone’s day!
Guess who might not die bitter and alone after all?!?
… yeah, no, that “bitter and alone” thing is definitely still happening.
Still, it just made my day to make someone else’s day for once.
Sincerely,
Calhoun

Dear… Whatever We Are,
I know we broke up and since then we’ve continued to say “I love you”, have sex, and hold hands.
Naturally, this area is a little- well, our footing is a little less than stable, isn’t it?
I wanna let it be known that I’m not pushing to DTR.
For you squares, that’s “define the relationship.”
Nope. Not me. I’m super easy-going.
Okay, none of us were buying that… still, I’m not pushing you to define what we are because, truth be told, I love you but I think you nee to be okay on your own before we can be a serious version of whatever we are.
But last night? Last night we crossed a boundary. We’re talking serious dating territory.
Last night… you farted.
We’ve talked about this before. When we broke up or whatever, we agreed sex was still on the table and farting was permanently off the table. You said that. You broke your own rule.
I’m sorry, I’ll put up with a lotta stuff, but if you’re farting in front of me?
Yeah, that’s the uncomfortably comfortable territory of dating.
Your move, buddy.
Sincerely,
Calhoun

PS I totally don’t think it’s weird that, according to me, the progression of our relationship is marked by flatulence. Not weird at all.

Dear Futurama,
Thanks for that. Pretty sure I have no salt left in my system from bawling at your series finale last night.
Nah, you couldn’t just, like, let this one go, could you?
No, what’s the fun in that? How about a little emotional devastation?!?
You know I connect better to television than real life!
It’s part of why I’m so charmingly emotionally stunted at my age.
But after last night? Yeah, fuck that, I’m goin’ back to being all-around dead inside.
Sincerely,
Calhoun